Freddy Woo writes, "aged eight, a boy from my class told me everything these was to know about sex: male prostitutes are called destitutes and women use tampons to stop men sticking their willies up them. Also, women pee out their bums, something I didn't realise was wrong until I was about 18 and my first girlfriend looked at me aghast."

Three's a crowd
My sex misconception was that having my first threesome would be a good idea.

It didn’t happen by accident. One of my best mates, let’s call him Darren, had a girlfriend who was liberal to the point of having no inhibitions whatsoever. This suited Darren perfectly and he used to boast to me regularly about the latest perversion they’d tested in the bedroom (or the kitchen, or the park… you get the idea).

I was midway through Uni at the time but Darren and I had been friends all the way through school, been in sports teams together and it’s fair to say we knew each other about as well as two guys can, or so I thought. His girlfriend Jenny was a couple of years older than us but we’d both known her at school too. She was a stunning girl and great fun but unashamedly also a sexual deviant.

The night of Darren’s birthday was when it happened. We were all a bit drunk and in no mood to stop when the music at the nightclub finished, so it was decided to go back to their house to continue the party. In the back of the cab, Jenny in the middle and Darren and me on either side, it became clear I was in for more than I’d bargained when she started groping me. A quick glance to the left revealed that Darren was already getting a hand job. He turned to me and said “Jenny’s always fancied a threes-up with you and me, how about it?”.

Well, what could I say? Nothing, as it happened. She winked at me, I smiled nervously in reply and she unbuttoned my flies with her free hand …

After an awkward payment to the blushing cabbie, we piled into their house and into the living room. I had no idea what to expect, it felt like losing my virginity again. She dabbled with the idea of just getting down to it right there, but Darren pointed out that the bedroom would be more comfortable. Our trio of bodies gradually made its way through the hallway and up the stairs, Jenny occasionally stopping to lick or fondle our various body parts. By the time we arrived at the bedroom, our clothes were all over the house.

I let Jenny dictate the pace when she wasn’t using her skills on Darren as I really didn’t know what I was doing; I’d had plenty of solo partners myself but this was my first ménage-a-trois so I didn’t want to overstep whatever boundaries remained. Nevertheless, trying to be passive and gentlemanly in such rare circumstances just doesn’t work.

Growing bored of switching attention back and forth between our respective cocks, Jenny commanded Darren to fuck her hard, and he happily obliged. While he was busily shagging her from behind, I decided to engage in a bit of ‘spit roasting’, then she insisted that we swap ends. It was certainly a weird feeling to be fucking my best mate’s girl while he was being fellated by her a couple of feet away, watching my every thrust intently. It was all a bit surreal and I didn’t think it would go any further, but Jenny wanted to try every conceivable position available to the three of us. She laid me on the bed, straddled me and invited Darren to fill her vacant rear entrance. It turns out that double penetration is much more difficult than porn movies would have you believe.

After an unenjoyable sojourn into shitty city, Darren decided it was time to watch me and Jenny for a bit while he “cleaned himself off”… yuck. I was still lying on the bed so Jenny assumed the classic ‘69’ position and began giving me a very fine blowjob while I got to work on her. Darren couldn’t stand just watching so after a few cursory wipes he decided to resume his previous position in Jenny’s wrong ‘un, which was fine for him. However, it placed me in the unenviable position of having to look directly up at his sweaty ballsack and arse. I closed my eyes and tried to concentrate on Jenny’s excellent technique rather than my best friend’s pendulous undercarriage slamming into her chocolate exit strategy.

With my eyes closed, I was finally starting to enjoy the experience myself. I could feel the pressure building as Jenny demonstrated her lack of a meaningful gag reflex and could tell she was enjoying my oral generosity too. She was really wet to the point of dripping into my mouth, so I lapped it up like a dog eating a melted ice cream. I’d never experienced anything like it before, but it was a real turn on to know she was getting so much pleasure, even if she did taste a bit different to most of the girls I’d been with before. After another minute or two she finished me off in her mouth. Feeling rather exhausted and self conscious again, I opened my eyes again only to find that Darren was already lying next to us. Confused, I looked up and noticed a trickle of light brown fluid running from Jenny’s fudge box, all the way down her lady-garden and stretching onto my own lips.

Unfortunately for me, while I had been lost in mutual oral pleasure with my eyes closed, Darren had quietly emptied a remarkable load of hot monkey custard into Jenny’s backside, and then he’d pulled out with predictable results. It wasn’t my tongue that had made her beef pocket so impressively moist after all. The worst part was that I’d swallowed most of the devil’s own cocktail in the mistaken belief that it was my prize for being so good at cunnilingus. I ended up blaming the ensuing bout of puking on the evening’s drinks.

So kids, my advice to you is: if you ever end up being asked to a threesome, for goodness’ sake, either get the boy/girl ratio right or ensure that gravity is on your side.

Apologies if the ending to this tale has left a nasty taste in your mouth too.
(chart cathas an itch, Wed 1 Oct 2008, 11:28,
73 replies)

Am I the only one not utterly repulsed by this? I must have a far stronger stomach than I realised (well, psychologically, a karahi chicken curry still has me farting like a trooper the day after, much to the chagrin of my work colleagues).
(jim_bobcan herd cats., Wed 1 Oct 2008, 11:36,
closed)

had I not seen the evidence slithering down her fanny
I probably wouldn't have even realised. I was a bit drunk too. I sobered up pretty bloody quickly though
(chart cathas an itch, Wed 1 Oct 2008, 13:05,
closed)

So...
am I the only person a little bit turned on by this then?
(Sonic James Doomforgetting the date since... umm..., Wed 1 Oct 2008, 13:33,
closed)

I doubt it
this is b3ta, after all.

btw: that story you posted a while back about the festival toilets and the bakewell tart... was it Glasto or T in the Park by any chance? I saw exactly the same thing at one of those festivals (back in 2004/2005 IIRC). A fitting garnish, I thought at the time
(chart cathas an itch, Wed 1 Oct 2008, 13:44,
closed)

Ha ha!
It was Reading in about 2000 I think... might have been 2003...

*it's a lie, I was hungry, but now I don't think I'll want to eat for a week.
(Moey, Wed 1 Oct 2008, 14:01,
closed)

Lovely story
lovingly told. Shocking ending!!!

I must be a bad man - I can imagine the cabbie driving off to a dark alley and having a quick one off the wrist in the back of the cab before cleaning it all up...
(Che GrimsdaleBest before:, Wed 1 Oct 2008, 14:02,
closed)

Interesting ending
I could see something bad was about to happen. I thought that it would be Darren's excited cock leaving Jenny's arse, and then being thrust deeply into the mouth that was licking Jenny's "beef pocket".
(turb0t, Wed 1 Oct 2008, 14:05,
closed)